Article
Chemistry, Physical
Sabrina Henche, Bettina M. Nestl, Bernhard Hauer
Summary: The Friedel-Crafts alkylation using squalene-hopene cyclases provides a biological alternative to traditional strategies for forming carbon-carbon bonds. These enzymes, particularly AacSHC from Alicyclobacillus acidocaldarius and its variants, have shown broad substrate and reaction scope, demonstrating potential applications in biocatalysis. Notably, the regioselectivity of the alkylation reaction and promiscuous activity in catalyzing hydration of substrates highlight the promise of enzymatic catalysis for selective C-C bond formations.
Article
Microbiology
Arijit Mukherjee, Hitesh Tikariha, Aditya Bandla, Shruti Pavagadhi, Sanjay Swarup
Summary: This study expands our understanding of the biosynthetic potential of phytobiomes by using a worldwide and extensive collection of microbiomes from plants and soil. It provides vital resources for plant microbiome researchers and insights into the evolution of biosynthetic gene clusters (BGCs) in phytobiomes under the influence of plant hosts. The study reveals the varying strengths of phylogenetic conservation in different classes of BGCs and the deep conservation of biosynthetic potential in specialized metabolites. It also identifies potentially novel classes of metabolites in the most conserved class of specialized metabolites (terpenes).
Review
Biotechnology & Applied Microbiology
Indu Muraleedharan Nair, Jayachandran Kochupurackal
Summary: Squalene hopene cyclases (SHC) convert squalene to hopanoid, which plays a crucial role in maintaining membrane fluidity and stability in bacteria. Their analogues, 2,3-oxido squalene cyclases, have also been studied for their stereo selectivity and efficiency. The ability of squalene hopene cyclase to accommodate non-natural substrates can be utilized in industrial applications. This review focuses on the cloning and overexpression strategies of squalene hopene cyclase, as well as recent research on using non-natural molecules as substrates for squalene cyclase mediated cyclization reactions of flavor and pharmaceutical significance.
BIOTECHNOLOGY LETTERS
(2023)
Article
Chemistry, Physical
Kristina Schell, Heng Li, Lukas Lauterbach, Kizerbo A. Taizoumbe, Jeroen S. Dickschat, Bernhard Hauer
Summary: This study demonstrates a simple structure-guided strategy to create alternative active site confinement in the squalene-hopene cyclase enzyme. By modifying the substrate tunnel to increase proximity between the substrate and catalytic site, the enzyme's catalytic efficiency was significantly improved.
Review
Agriculture, Multidisciplinary
Eric Eichhorn, Fridtjof Schroeder
Summary: (-)-Ambrox is the main olfactive component of ambergris and a widely used biodegradable fragrance ingredient. Traditionally, it is synthesized from the diterpene sclareol through chemical steps. The availability of (E)-beta-farnesene as a new feedstock opened up new pathways for the production of (-)-ambrox. This review discusses the potential of biotechnology in developing a more sustainable process for the industrial production of (-)-ambrox and traces back to the origin of ambergris and the discovery of (-)-ambrox as its main olfactive principle.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Physical
Andreas Schneider, Jacqueline Ruppert, Thomas B. Lystbaek, Silke Bastian, Bernhard Hauer
Summary: Here, we demonstrate the modification of the cation cage of Squalene-hopene cyclases (SHCs) to achieve an enantioselective semipinacol rearrangement of bicyclic allylic alcohols, producing valuable oxa-carbon spirocyclic compounds. Through structure-guided semirational engineering, we designed a biocatalyst with high catalytic performance (approximately 4500 TTN) and excellent enantioselectivity (99.5% enantiomeric excess, ee). In silico studies indicate that a broadened active site is crucial for catalysis. This study highlights the potential of harnessing the SHC's cation cage for asymmetric Bronsted-acid catalysis.
Article
Biochemistry & Molecular Biology
Jun-ichi Tamura, Takahiro Tamura, Shunsuke Hoshino, Rieko Imae, Ryuichi Kato, Mizuki Yokono, Mao Nagase, Shiho Ohno, Noriyoshi Manabe, Yoshiki Yamaguchi, Hiroshi Manya, Tamao Endo
Summary: Ribitol phosphate modifications to the core M3 O-mannosyl glycan play a crucial role in the functional maturation of alpha-dystroglycan. The study reveals that ribitol phosphate transferase catalyzes the transfer of ribitol phosphate and subsequent glycosylation reactions mediated by a series of glycosyltransferases.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Eric Eichhorn, Corinne Baumgartner, Marc Biermann
Summary: In order to support perfumers in creating unique and instantly recognizable perfumes, there is a continuous need for developing new odorant molecules and processes. Givaudan emphasizes the importance of sustainability in both molecules and processes, and biocatalysis has the potential to positively influence these aspects. This review highlights the application of oxidoreductase and isomerase enzymes at Givaudan for the production of odorant molecules at both laboratory and industrial scale.
Review
Biochemistry & Molecular Biology
Jack J. Sangster, James R. Marshall, Nicholas J. Turner, Juan Mangas-Sanchez
Summary: Organic chemistry provides society with essential products, but concerns about the environmental impact of the chemical industry are driving changes in manufacturing. Biocatalysis, using enzymes as catalysts, offers a sustainable alternative with high selectivity and mild reaction conditions. Advances in molecular biology, bioinformatics, and chemical engineering have expanded the range of available transformations in biocatalysis.
Review
Biochemistry & Molecular Biology
Kuan Chen, Meng Zhang, Min Ye, Xue Qiao
Summary: This review summarizes 98 mutation sites in 25 plant OSCs and identifies conserved key residues through sequence alignment, while discussing structure-function relationships. Substrate selectivity is also summarized to probe the active site cavity of plant OSCs.
NATURAL PRODUCT REPORTS
(2021)
Article
Biochemistry & Molecular Biology
Shusuke Sato, Fumitaka Kudo, Michel Rohmer, Tadashi Eguchi
Summary: Adenosylhopane is a crucial precursor of C-35 hopanoids, formed through a crosslinking reaction catalyzed by the HpnH enzyme. The involvement of conserved cysteine residues in ZmHpnH suggests a role in the formation of radical intermediates at the C22 position, leading to the stereoselective conversion of diploptene. These findings provide important insights into the biosynthesis mechanism of hopanoids.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
